1.1: potassium carbonate; methanol / 2 h / 20 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / |Inert atmosphere 2.2: 0.5 h / 20 °C / |Inert atmosphere 3.1: hydrogen; palladium 10 on activated carbon / ethyl acetate / 15001.5 Torr 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 5.1: triethylamine / dichloromethane / 0.5 h / 0 °C / |Inert atmosphere 6.1: sodium iodide / acetone / 0.25 h / 20 °C 7.1: N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 8.1: sodium hydroxide; water / 4 h / |Reflux View Scheme

1.1: potassium carbonate; methanol / 2 h / 20 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / |Inert atmosphere 2.2: 0.5 h / 20 °C / |Inert atmosphere 3.1: hydrogen; palladium 10 on activated carbon / ethyl acetate / 15001.5 Torr 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere View Scheme

Stage #1: With  potassium hydroxide in  methanol T=10 - 20°C; 0.0833333 h; Stage #2: With  acetic acid in  methanol Show Experimental Procedure  

Multi-step reaction with 5 steps 1.1: potassium carbonate; methanol / 2 h / 20 °C / |Inert atmosphere2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / |Inert atmosphere2.2: 0.5 h / 20 °C / |Inert atmosphere3.1: hydrogen; palladium 10 on activated carbon / ethyl acetate / 15001.5 Torr4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere5.1: triethylamine / dichloromethane / 0.5 h / 0 °C / |Inert atmosphere